EP0189085A2 - Agents tensio-actifs cationiques à base de composés d'ammonium quaternaire et leur utilisation dans les compositions pour nettoyage - Google Patents

Agents tensio-actifs cationiques à base de composés d'ammonium quaternaire et leur utilisation dans les compositions pour nettoyage Download PDF

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Publication number
EP0189085A2
EP0189085A2 EP86100364A EP86100364A EP0189085A2 EP 0189085 A2 EP0189085 A2 EP 0189085A2 EP 86100364 A EP86100364 A EP 86100364A EP 86100364 A EP86100364 A EP 86100364A EP 0189085 A2 EP0189085 A2 EP 0189085A2
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EP
European Patent Office
Prior art keywords
cationic surfactants
carbon atoms
quaternary ammonium
ammonium compounds
general formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP86100364A
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German (de)
English (en)
Other versions
EP0189085B1 (fr
EP0189085A3 (en
Inventor
Jürgen Dr. Geke
Horst Dr. Rutzen
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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Publication date
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Priority to AT86100364T priority Critical patent/ATE56698T1/de
Publication of EP0189085A2 publication Critical patent/EP0189085A2/fr
Publication of EP0189085A3 publication Critical patent/EP0189085A3/de
Application granted granted Critical
Publication of EP0189085B1 publication Critical patent/EP0189085B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium compounds

Definitions

  • the invention relates to new, improved cationic surfactants based on quaternary ammonium compounds and the use of such cationic surfactants in industrial cleaning solutions.
  • DE-OS 27 12 900 and DE-OS 32 47 431 propose processes in which, in addition to other detergent components, quaternary ammonium compounds are used as cationic surfactants in the alkaline pH range, in which ammonium is used. Nitrogen atom organic radicals, especially alkyl radicals of different chain lengths, are bound.
  • Counterions of the ammonium cations used are, for example, anions such as chloride, sulfate or methyl sulfate, which are known as anions which cause corrosion.
  • the necessary content of such anions undesirably promotes corrosion on system parts and treated metal surfaces. This is an extremely disadvantage, in particular when treating metal surfaces with aqueous products, in particular when higher application concentrations of cationic surfactants are desired. Corrosion occurs not only in the long term during the intermediate storage of treated parts, but also directly when treating corresponding surfaces with the aqueous application solutions.
  • DE-OS 30 48 642 also discloses surfactant mixtures for cleaning bottles and other objects with hard surfaces (porcelain, plastic, metal) which contain cationic surfactants based on ammonium compounds.
  • cationic surfactants based on ammonium compounds.
  • a disadvantage of these surfactants is that they contain chloride, bromide or methyl sulfate as anions. In this case, too, the anions counteract the desired corrosion protection on system parts (e.g. dishwashers) and treated surfaces as a result of the treatment with such surfactant mixtures.
  • the object of the present invention was therefore to provide new, improved cationic surfactants based on quaternary ammonium compounds, which Not have disadvantages from the prior art.
  • cationic surfactants should be made available for industrially usable cleaning agents, the components of which inhibit the corrosion process, ensure a sufficient demulsifying effect with regard to anionic contamination and can be readily packaged in aqueous industrial cleaners, ie are easily water-soluble, do not cause any troublesome precipitations and with others Components commonly used in industrial cleaners are compatible.
  • the object is achieved by new, improved cationic surfactants based on quaternary ammonium compounds, the ammonium nitrogen atom of which carries at least two alkyl radicals, a 2-hydroxyalkyl radical originating from the reaction with a terminal epoxide carrying 10 to 24 carbon atoms and optionally an arylalkyl group and the like
  • Anion is the anion of an organic carboxylic acid with 5 to 16 carbon atoms.
  • cationic surfactants not only have good demulsifying properties with regard to anionic surfactants or emulsifiers, but also make the treated surfaces hydrophobic in corresponding industrial cleaners, and help prevent corrosion by ensuring that the application liquids run off the treated surfaces well and without running and even an antistatic effect can be achieved on plastic surfaces.
  • linear or branched alkyl radicals which R 1 and R 2 can represent are methyl, ethyl, propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, tetradecyl and hexadecyl.
  • Quaternary ammonium compounds in which R 2 is hydrogen and R 1 is a linear or branched alkyl radical having 8 to 22 carbon atoms for example n-octyl, n-decyl, n-dodecyl, n-tetradecyl or n-hexadecyl, are preferred.
  • the total number of carbon atoms in both substituents R 1 and R 2 must be in the range from 8 to 22 carbon atoms.
  • the R 5 radical bonded to the ammonium nitrogen atom represents alkyl radicals such as, for example, n-butyl, i-butyl, tert-butyl, n-pentyl, tert-butylmethyl or n-hexyl or phenalkyl radicals such as benzyl, phenylethyl or phenylpropyl.
  • the counter anion in the cationic surfactants according to the invention is the anion of an organic carboxylic acid having 5 to 16 carbon atoms, ie the radical R 6 in the general formula I represents alkyl radicals such as, for example, n-butyl, i-butyl, tert-butyl, pentyl, Hexyl, octyl, 2-ethyl-hexyl, n-nonyl, i-nonyl, decyl, dodecyl or pentadecyl.
  • the isononanoate anion is particularly preferred.
  • the compounds of the general formula I according to the invention can be prepared by methods known per se by adding the salt of a tertiary amine of the general formula in which R 3 , R 4 and R 5 have the meanings given above have, and an organic acid of the general formula in which R 6 has the meaning given above, in water with an epoxy compound of the general formula in which R 1 and R 2 have the meanings given above and together have a number of C atoms in the range from 8 to 22, in a stoichiometric ratio at normal pressure and a temperature between 40 and 100 ° C, the reaction mixture before the start Implementation has a pH of at least 7.
  • the epoxides of the general formula IV used to prepare the quaternary ammonium compounds according to the invention can thus be epoxides having 10 to 24 carbon atoms in which the oxirane ring is located at any point in the molecule.
  • the amines used to prepare the quaternary ammonium compounds of the general formula I are preferably tertiary alkyl, hydroxyalkyl or alkylarylamines, with dimethylbutylamine and dimethylbenzylamine being particularly preferred.
  • the carboxylic acids used to prepare the quaternary ammonium compounds according to the invention are preferably monocarboxylic acids having 5 to 8 carbon atoms in the alkyl radical. Isononanoic acid is particularly preferably used.
  • the quaternary ammonium compounds according to the invention are used as cationic surfactants in industrial cleaning solutions. They have the advantage over other cationic surfactants as well as quaternary ammonium compounds already known from the prior art that they do not contain any corrosive counterions or lead to undesirable precipitations.
  • the anions of the organic acid used for the production of the ammonium compounds according to the invention are even able to inhibit the corrosion process on cleaned metal surfaces.
  • the lack of accumulation of corrosive anions in the baths and the inhibitory effect of the carboxylic acid anions thus improve the corrosion protection properties in aqueous media. This applies equally to parts that have to be temporarily stored before the further processing process, as well as to parts that are to be processed immediately.
  • the improved corrosion protection is particularly noticeable in those parts - which have been treated with industrial cleaners containing quaternary ammonium compounds - and which have a creative effect due to their geometry.
  • industrial cleaners containing quaternary ammonium compounds - Using conventional cleaners K was orrosionsgefahr particularly great, since evaporation of the solvent, was feared as a rule water, a strong enrichment of the ingredients and thus the corrosive constituents on such parts. This is when using the quaternary ammonium compounds according to the invention prevented as industrial cleaning solutions containing cationic surfactants.
  • the cationic surfactants according to the invention offer a further advantage in that an advantageous hydrophobization of the cleaned surfaces, in particular the cleaned metal surfaces, is observed. Furthermore, corrosion of the treated parts is avoided by a very good drainage behavior of the application liquid.
  • aqueous industrial cleaning solutions which contain the quaternary ammonium compounds according to the invention as cationic surfactants can also be used for cleaning plastics, since they have an antistatic effect. It is precisely this that will open up such products to a wide range of applications in the future, since plastic surfaces, similar to metal surfaces, are being cleaned with an increasing tendency in spray processes.
  • the quaternary ammonium compounds according to the invention are suitable for use in all cleaning agents which are important for industrial cleaning. They can be used in sprayable cleaners, e.g. neutral to weakly alkaline cleaners or acid cleaners may be present, especially in cleaning solutions that are sprayed onto the parts to be cleaned under high pressure. Equally, however, they can also be used with advantage in immersion cleaners based on nonionic surfactants.
  • Quaternary ammonium compounds according to the invention are also used as cationic surfactants which act as demulsifiers or antifoams in industrial cleaning solutions for spraying or dipping.
  • the new, improved cationic surfactants based on quaternary ammonium compounds are made up with other components, which are conventional for industrial cleaning solutions, using processes known per se.
  • these solutions may also contain other additives, e.g. contain alkanolamines, phosphates, borates or nitrites.
  • inhibitors in particular for non-ferrous metals, or biocides such as, for example, hexahydrotriazine derivatives and / or phenols and / or chlorophenols to prevent bacterial and / or fungal attack in the spraying or immersion systems can also be added to the solutions.
  • the cleaning agents formulated as described above could easily be applied by spraying. They showed little or no tendency to foam. The cleaning baths were stable for a long time and their cleaning power did not deteriorate over this time. Due to the use of the quaternary ammonium compounds according to the invention, the metal surfaces treated with the cleaners in spraying did not corrode, but instead had increased corrosion protection in comparison with treatment with conventional cleaners.
  • the cleaning agents formulated as described above had a high cleaning power on treated metal surfaces over a long period of time and their baths were very stable. Metal surfaces that had been treated with the above-described cleaners in immersion had improved corrosion protection compared to metal surfaces treated with conventional cleaners.
  • the emulsion cleavage was carried out according to the following test: 10 g of drilling oil were emulsified at room temperature with 40 g of a 2% aqueous neutral cleaning solution in a 270 ml oil separation flask. An equivalent amount of BDHAI was added. The mixture was filled with 2% hot neutral cleaning solution while shaking. Demulsification started spontaneously. For complete oil separation from the initially "emulsion-like phase", the liquid was tempered at 80 ° C. for two hours.
  • the returned cleaning solution could be sprayed foam-free.
  • General cleaning agents e.g. cleaning agents for vehicles, cleaning agents for walls and floors of industrial companies and products for steam jet cleaning; application concentrations in the range from 2 to 30%
  • the cleaning compositions composed as described above showed good cleaning action and a uniform, run-free drainage behavior on the treated parts.
  • BDHAI shows a significantly better corrosion protection behavior.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
EP86100364A 1985-01-21 1986-01-13 Agents tensio-actifs cationiques à base de composés d'ammonium quaternaire et leur utilisation dans les compositions pour nettoyage Expired - Lifetime EP0189085B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT86100364T ATE56698T1 (de) 1985-01-21 1986-01-13 Neue kationtenside auf der basis von quartaeren ammoniumverbindungen und ihre verwendung in reinigungsmitteln.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19853501775 DE3501775A1 (de) 1985-01-21 1985-01-21 Neue kationtenside auf der basis von quartaeren ammoniumverbindungen und ihre verwendung in reinigungsmitteln
DE3501775 1985-01-21

Publications (3)

Publication Number Publication Date
EP0189085A2 true EP0189085A2 (fr) 1986-07-30
EP0189085A3 EP0189085A3 (en) 1987-02-25
EP0189085B1 EP0189085B1 (fr) 1990-09-19

Family

ID=6260296

Family Applications (1)

Application Number Title Priority Date Filing Date
EP86100364A Expired - Lifetime EP0189085B1 (fr) 1985-01-21 1986-01-13 Agents tensio-actifs cationiques à base de composés d'ammonium quaternaire et leur utilisation dans les compositions pour nettoyage

Country Status (9)

Country Link
US (1) US4678605A (fr)
EP (1) EP0189085B1 (fr)
JP (1) JPS61192330A (fr)
AT (1) ATE56698T1 (fr)
AU (1) AU579443B2 (fr)
BR (1) BR8600200A (fr)
CA (1) CA1259011A (fr)
DE (2) DE3501775A1 (fr)
ZA (1) ZA86412B (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0249164A1 (fr) * 1986-06-13 1987-12-16 Henkel Kommanditgesellschaft auf Aktien Agents tensio-actifs cationiques basés sur des composés d'ammonium quaternaires et leur application comme détergents
WO1989009204A1 (fr) * 1988-04-02 1989-10-05 Henkel Kommanditgesellschaft Auf Aktien Composes quaternaires d'ammonium
EP0345475A1 (fr) * 1988-05-13 1989-12-13 Hoechst Aktiengesellschaft Procédé de production de sels d'ammonium quaternaires d'acides carboxyliques de chaîne aliphatique longue
EP2604674A1 (fr) * 2011-12-12 2013-06-19 Basf Se Utilisation d'alkylamine quaternisé comme additif dans des carburants et des lubrifiants

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4001595A1 (de) * 1990-01-20 1991-07-25 Henkel Kgaa Demulgierende, pulverfoermige oder fluessige reinigungsmittel und deren verwendung
US5096610A (en) * 1990-11-06 1992-03-17 Atochem North America, Inc. Floor finish remover compositions
US5202049A (en) * 1990-11-06 1993-04-13 Elf Atochem North America, Inc. Sealer finish remover compositions
DE4334368C2 (de) * 1993-10-08 1995-12-14 Henkel Kgaa Schwach schäumende polymerfreie Reinigungsmittel
AU7401498A (en) * 1996-12-06 1998-06-29 Henkel Corporation Composition and method for cleaning/degreasing metal surfaces, especiall y composites of copper and aluminum
US5824163A (en) * 1997-02-28 1998-10-20 Henkel Corporation Metal cleaning process that does not damage plastic
DE10141707B4 (de) * 2001-08-25 2008-07-24 Chemetall Gmbh Verfahren zur antistatischen Beschichtung von Kunststoff-Formteil-Oberflächen, von mit Kunststoff oder/und Lack beschichteten Formteilen und Verwendung der nach den Verfahren behandelten Kunststoff- oder/und Lackoberflächen
WO2007063691A1 (fr) * 2005-11-29 2007-06-07 Sanyo Chemical Industries, Ltd. Agent bacteriolytique
CA2632231C (fr) * 2005-12-02 2012-06-26 Baker Hughes Incorporated Inhibition de solides a base de naphtenate et d'emulsions dans le petrole brut
US8110707B2 (en) * 2007-12-14 2012-02-07 Aisin Aw Co., Ltd. Surfactant
WO2010017575A1 (fr) * 2008-08-11 2010-02-18 M-I Australia Pty Ltd Compositions et procédés d’inhibition de la formation d’émulsion dans des corps d’hydrocarbure
US20180110220A1 (en) * 2016-10-21 2018-04-26 Ecolab Usa Inc. Reduced inhalation hazard of quaternary ammonium compounds-ph driven physiological response

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2759975A (en) * 1952-05-28 1956-08-21 Gen Aniline & Film Corp Mixed alkyl-benzyl-alkylol quaternary ammonium salts
DE2631733A1 (de) * 1975-07-29 1977-02-10 Air Prod & Chem Verfahren zur foerderung von kondensations- und/oder polymerisationsreaktionen von organischen isocyanaten
EP0012215A1 (fr) * 1978-11-11 1980-06-25 BASF Aktiengesellschaft Sel de choline et d'acide hydroxy-2-butane sulfonique et son utilisation comme sel conducteur

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3636114A (en) * 1968-07-16 1972-01-18 Union Carbide Corp Novel quaternary ammonium compounds and method for preparation thereof
BE793339A (fr) * 1970-10-20 1973-06-27 Henkel & Cie Gmbh Agent de traitement complementaire du linge et son procede de preparation
DE2712900C2 (de) * 1977-03-24 1986-04-10 Henkel KGaA, 4000 Düsseldorf Verfahren zur Reinigung von Metallen im Spritzverfahren
DE3048642A1 (de) * 1980-12-23 1982-07-15 Hoechst Ag, 6000 Frankfurt "tensidgemisch zur reinigung harter oberlaechen"
DE3246124A1 (de) * 1982-12-13 1984-06-14 Henkel KGaA, 4000 Düsseldorf Reinigungsverfahren
DE3247431A1 (de) * 1982-12-22 1984-06-28 Henkel KGaA, 4000 Düsseldorf Verfahren zur regenerierung bzw. zum recycling von waessrigen entfettungs- und reinigungsloesungen
DE3321608A1 (de) * 1983-06-15 1984-12-20 Henkel KGaA, 4000 Düsseldorf Verfahren zur herstellung von quartaeren ammoniumverbindungen
US4595526A (en) * 1984-09-28 1986-06-17 Colgate-Palmolive Company High foaming nonionic surfacant based liquid detergent

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2759975A (en) * 1952-05-28 1956-08-21 Gen Aniline & Film Corp Mixed alkyl-benzyl-alkylol quaternary ammonium salts
DE2631733A1 (de) * 1975-07-29 1977-02-10 Air Prod & Chem Verfahren zur foerderung von kondensations- und/oder polymerisationsreaktionen von organischen isocyanaten
US4040992A (en) * 1975-07-29 1977-08-09 Air Products And Chemicals, Inc. Catalysis of organic isocyanate reactions
EP0012215A1 (fr) * 1978-11-11 1980-06-25 BASF Aktiengesellschaft Sel de choline et d'acide hydroxy-2-butane sulfonique et son utilisation comme sel conducteur

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0249164A1 (fr) * 1986-06-13 1987-12-16 Henkel Kommanditgesellschaft auf Aktien Agents tensio-actifs cationiques basés sur des composés d'ammonium quaternaires et leur application comme détergents
US4814108A (en) * 1986-06-13 1989-03-21 Henkel Kommanditgesellschaft Auf Aktien Cationic surfactants based on quaternary ammonium compounds and use thereof in cleaning agents
WO1989009204A1 (fr) * 1988-04-02 1989-10-05 Henkel Kommanditgesellschaft Auf Aktien Composes quaternaires d'ammonium
EP0336267A2 (fr) * 1988-04-02 1989-10-11 Henkel Kommanditgesellschaft auf Aktien Composés d'ammonium quaternaires
EP0336267A3 (fr) * 1988-04-02 1989-10-25 Henkel Kommanditgesellschaft auf Aktien Composés d'ammonium quaternaires
EP0345475A1 (fr) * 1988-05-13 1989-12-13 Hoechst Aktiengesellschaft Procédé de production de sels d'ammonium quaternaires d'acides carboxyliques de chaîne aliphatique longue
EP2604674A1 (fr) * 2011-12-12 2013-06-19 Basf Se Utilisation d'alkylamine quaternisé comme additif dans des carburants et des lubrifiants
WO2013087701A1 (fr) * 2011-12-12 2013-06-20 Basf Se Utilisation d'alkylamines quaternisées en tant qu'additifs de carburants et de lubrifiants
EP4219667A3 (fr) * 2011-12-12 2023-08-16 Basf Se Utilisation d'alkylamines quaternisées comme additifs dans des carburants et des lubrifiants

Also Published As

Publication number Publication date
EP0189085B1 (fr) 1990-09-19
JPS61192330A (ja) 1986-08-26
US4678605A (en) 1987-07-07
AU579443B2 (en) 1988-11-24
ATE56698T1 (de) 1990-10-15
ZA86412B (en) 1986-09-24
CA1259011A (fr) 1989-09-05
DE3674216D1 (de) 1990-10-25
EP0189085A3 (en) 1987-02-25
DE3501775A1 (de) 1986-07-24
BR8600200A (pt) 1986-09-30
AU5247386A (en) 1986-07-24

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